Hollywood in the 1930s. Lillian Hellman (Judy Davis), a failed poet and aspiring screenplay writer meets and falls in love with Dashiell Hammett (Sam Shepard), an immensely successful crime novelist. The two of them go together like salt and pepper. He's a charming raconteur and she possesses a sharp wit.

Screenplay writer Jerry Ludwig presents 30 years of their turbulent relationship, which is constantly being reformed as they make adjustments for alcoholism, adultery, the pressures of celebrityhood, and their artistic idiosyncrasies. The drama depicts a role reversal as Hellman's fame as a playwright grows at a time when Dash's career as a writer is in decline. Both of them come under attack for their liberal politics during the 1950s witchhunts by the House Committee on Un-American Activities.

Also appearing in Dash and Lilly are Bebe Neuwirth as Dorothy Parker and David Paymer as Hellman's first husband. Kathy Bates directs this portrait of an unconventional but long-lasting love relationship.